One-pot domino synthesis of 4-heteroaryl-2-phenyl-quinazolines bearing 5-aryl-1,3-oxathiol-2-ylidene amine and substituted 1,3-thiazole groups

Abstract

The reaction of thioamides 1–5 with phenacyl halides offers the advantage of an efficient domino synthesis of the title 4-heteroaryl-2-phenylquinazolines bearing 1,3-oxathiol-2-ylidene amine 6a–d and 1,3-thiazoles 7–11. The reaction shows unexpected thermodynamic and kinetic control products. In the same manner, thioamides 1, 2 and 4 react with methyl chloroacetate to afford 4-[2-dialkylamino-4(5H)-oxo-1, 3-thiazol-5-yl]-2-phenyl-quinazolin-4(3H)-ylidene 12, 13 and 14, respectively. Similarly, 2-morpholino-5-(2-phenylquinazolin-4-yl)thiazol-4-amine 15 is formed by the reaction of 1 with chloroacetonitrile. Synthesized compounds were characterized on the basis of the well known reaction mechanisms elemental analysis, NMR, mass spectroscopy and X-ray data.

Keywords:

• 1,3-thiazoles
• 1,3-oxathioles
• thermodynamically controlled and kinetically controlled reactions
• domino reactions
• NK-3R antagonists
• 4-heteroaryl-2-phenyl-quinazolines